85107-38-6Relevant articles and documents
Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation
Deng, Xi,Guo, Jiandong,Su, Weiping,Wang, Xiaotai,Zhang, Xiaofeng
supporting information, p. 24510 - 24518 (2021/08/12)
The Ni-catalyzed decarbonylative borylation of (hetero)aryl carboxylic acids with B2cat2 has been achieved without recourse to any additives. This Ni-catalyzed method exhibits a broad substrate scope covering poorly reactive non-ortho-substituted (hetero)aryl carboxylic acids, and tolerates diverse functional groups including some of the groups active to Ni0 catalysts. The key to achieve this decarbonylative borylation reaction is the choice of B2cat2 as a coupling partner that not only acts as a borylating reagent, but also chemoselectively activates aryl carboxylic acids towards oxidative addition of their C(acyl)?O bond to Ni0 catalyst via the formation of acyloxyboron compounds. A combination of experimental and computational studies reveals a detailed plausible mechanism for this reaction system, which involves a hitherto unknown concerted decarbonylation and reductive elimination step that generates the aryl boronic ester product. This mode of boron-promoted carboxylic acid activation is also applicable to other types of reactions.
Metal-Free Radical Borylation of Alkyl and Aryl Iodides
Cheng, Ying,Mück-Lichtenfeld, Christian,Studer, Armido
, p. 16832 - 16836 (2018/11/23)
A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed.
Guest-encapsulation properties of a self-assembled capsule by dynamic boronic ester bonds
Nishimura, Naoki,Yoza, Kenji,Kobayashi, Kenji
, p. 777 - 790 (2010/04/01)
Two molecules of tetrakis(dihydroxyboryl)-cavitand 1a as an aromatic cavity and four molecules of 1,2-bis(3,4-dihydroxyphenyl)ethane 2 as an equatorial linker self-assemble into capsule 3a via the formation of eight dynamic boronic ester bonds in CDClsub